CN111440184B - Method for preparing high-purity carnosol - Google Patents
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Abstract
A method for preparing high-purity carnosol is provided. Dissolving herba Rosmarini officinalis extract with water saturated ethyl acetate; mixing the dissolved normal phase silica gel, loading the mixed solution into a column by a dry method, performing gradient elution by using chloroform, methanol and acetic acid (100-95) to (0-5) to (0-1 thousandth), combining the same components, and performing reduced pressure concentration to obtain carnosol with the purity of about 85%; and performing Sephadex LH-20 gel column chromatography purification, eluting the mobile phase with chloroform-methanol or petroleum ether-chloroform-methanol, mixing the same components, and evaporating under reduced pressure to dryness to obtain carnosol with purity of over 98%. The method can obtain high-purity carnosol with content of 98% or more from herba Rosmarini officinalis extract. The gel column can be used repeatedly, and has short column chromatography time and high efficiency. The method is simple, easy to operate, high in yield and suitable for large-scale production.
Description
The present application is a divisional application of the patent application "a method for simultaneously preparing high purity carnosol and carnosic acid from rosemary extract", original application No.: 201810092815.5, filing date originally: year 2018, month 1 and day 30.
Technical Field
The invention relates to a method for preparing high-purity natural antioxidant active ingredient carnosol from rosemary extract, in particular to a separation method of Sephadex LH-20 gel column chromatography with a remarkable effect on separating a large amount of carnosol.
Background
Rosemary is a natural antioxidant, and carnosol and carnosic acid are main antioxidant components of the rosemary, so that the demand of edible antioxidant products is increased along with the rapid development of the functional food industry; with the successful introduction of rosemary into China and large-area cultivation, the method for preparing the high-purity antioxidant active monomer from the rosemary or the extract thereof, which is simple, easy and cheap, is found, and has good use value and practical significance.
There are several patents reporting the extraction of antioxidant actives from rosemary: CN 1698587a reports a method for extracting rosemary total phenols, wherein the sum of the contents of the main components carnosol and carnosic acid is more than 13%; CN 101402864A, wherein the content of the main antioxidant active ingredients of carnosol and carnosic acid is more than 50 wt%; the content of carnosol and carnosic acid in the rosemary extract obtained from CN 105669432A is 40-45%. However, up to now, there are many patents reporting a method of obtaining high purity carnosic acid by separation and purification from rosemary only: CN 102115442A uses prepared phosphoric acid-silica gel column chromatography to obtain carnosic acid with the purity of 92%; CN 104058955A can be used for obtaining carnosic acid with purity of more than 98% by silica gel column chromatography; separating and purifying CN 101851158A by medium pressure chromatography, and recrystallizing with organic solvent to obtain carnosic acid with purity of 98%; CN 101113133A herba Rosmarini officinalis is extracted with weak base aqueous solution of disodium EDTA, the pH of the filtrate is adjusted with acid, the polarity of the filtrate is adjusted with organic solvent to obtain precipitate, and the precipitate is dried to obtain carnosic acid with purity of 99.42%. There are also methods for obtaining carnosol only by isolation and purification from rosemary: purifying CN 103319495A with macroporous adsorbent resin to obtain crude carnosol, and crystallizing with hydrophilic organic solvent to obtain carnosol with purity of 95%; CN 102171217A is prepared by crystallizing herba Rosmarini officinalis extractive solution with acetic acid at a certain ratio to obtain carnosol with purity of 85.6%; patent CN 101835782A and patent CN 101835783 a report that carnosol with purity of more than 90% is obtained by using a method for catalyzing the production of carnosol from carnosic acid.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a method for preparing large quantities of high-purity carnosol, which is simple, easy to operate, high in yield and suitable for large-scale production.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method of preparing high purity carnosol, the method comprising the steps of:
I. dissolving herba Rosmarini officinalis extract with water saturated ethyl acetate, filtering, and removing insoluble substances;
mixing the filtrate with normal phase silica gel, loading the mixture into a column by a dry method, loading the mixture by a dry method, performing gradient elution by chloroform, methanol and acetic acid (100-95): (0-5): (0-1 per thousand) (volume ratio), and combining the same components to obtain 5 components, wherein the components are respectively as follows: a small polar impurity part, a carnosol crude product, a carnosic acid crude product, a component with the main component of ursolic acid and a large polar impurity part;
and III, purifying the crude carnosol obtained in the step I by using hydroxypropyl sephadex, eluting a mobile phase by using chloroform to methanol (2-2.5) to 1 (volume ratio) or petroleum ether to chloroform to methanol (2-5) to 1 (volume ratio) at equal degrees, combining the same components, and evaporating to dryness under reduced pressure to obtain the carnosol with the content of more than or equal to 98%.
The method as described above, preferably, the rosemary extract is an ethanol aqueous extract of rosemary flowers or leaves.
The method as described above, preferably, the rosemary extract is extracted by the following method: the preparation method comprises the steps of crushing rosemary flowers or leaves, carrying out ultrasonic extraction on the rosemary flowers or leaves by using 50-70% ethanol aqueous solution according to the liquid-material ratio of (10-15) to 1(L/Kg) for 60-90 minutes for 2-4 times, combining extracting solutions, and carrying out reduced pressure concentration and evaporation to dryness to obtain the rosemary extract.
The method as described above, preferably, the gradient elution in step I is carried out five times, and the mobile phase is sequentially: chloroform; chloroform, methanol and acetic acid, the volume ratio is 100: 0: 1 per mill; chloroform, methanol and acetic acid in the volume ratio of 100 to 1; chloroform, methanol and acetic acid, the volume ratio is 100: 2: 1 per mill; chloroform, methanol and acetic acid, the volume ratio is 95: 5: 1 per mill.
In the method, the length of the hydroxypropyl glucan gel column in the step II is preferably 120-150 cm; loading columns by a wet method, and loading samples by the wet method; the flow rate of the mobile phase in the hydroxypropyl dextran gel is 2-6 ml/min.
Preferably, the ratio of chloroform to methanol in step II is 2.5: 1 (by volume), or the ratio of petroleum ether to chloroform to methanol is 5: 1 (by volume).
The invention has the beneficial effects that: the method only uses the normal phase silica gel adsorption column once, thereby not only removing the adsorptive pigment impurities in the sample, but also avoiding the loss of the sample caused by dead adsorption due to repeated sample loading of the normal phase silica gel. The Sephadex LH-20 gel does not adsorb the separated sample and can be repeatedly used for many times. The method is simple and feasible to operate, and is suitable for large-scale production of carnosol with the content of more than or equal to 98% by using the rosemary extract.
Drawings
FIG. 1 is a high purity carnosol HPLC assay;
FIG. 2 shows carnosol1H-NMR chart;
FIG. 3 is carnosol13C-NMR chart;
Detailed Description
EXAMPLE 1 preparation of Rosmarinus officinalis extract
10Kg of dried rosemary leaves are crushed and sieved by a 20-mesh sieve, the solvent is ultrasonically extracted by using 60 percent ethanol water solution by volume percentage concentration, and the liquid-material ratio is 12: 1(L/Kg), and the ultrasonic time is 75 min. Continuously extracting for three times, mixing extractive solutions, concentrating under reduced pressure, and evaporating to dryness to obtain herba Rosmarini officinalis extract with carnosol content of 10.28 wt%.
Example 2 preparation of high purity carnosol from Rosmarinus officinalis extract
Normal phase silica gel column separation and purification
500g of the rosemary extract prepared in example 1 was added to 5000ml of ethyl acetate saturated with water, dissolved by sonication for 0.5 hour, and the insoluble matter was removed by filtration. The filtrate was mixed with 500g of normal phase silica gel (160-. Gradient elution was performed, with the following mobile phases and extracts, in order of elution:
(1) the mobile phase is chloroform, the elution volume is 5L, and the elution components are mainly small polar impurity parts;
(2) the mobile phase comprises chloroform, methanol and acetic acid, and the volume ratio is 100: 0: 1 per mill, the elution volume is 10L, and the main component is carnosol with the content of about 85 percent;
(3) the mobile phase comprises chloroform, methanol and acetic acid, and the volume ratio is 100: 1: 1 per mill, the elution volume is 15L, and the main component is carnosic acid with the content of 90 percent;
(4) the mobile phase comprises chloroform, methanol and acetic acid, and the volume ratio is 100: 2: 1 per mill, the elution volume is 10L, and the main component is ursolic acid;
(5) the mobile phase comprises chloroform, methanol and acetic acid, and the volume ratio is 95: 5: 1 per mill, the elution volume is 5L, and the main component is a large polar impurity part.
Mixing the same components, recovering solvent under reduced pressure to obtain 1.2g of carnosol with content of 98% or more, and separating the carnosol with content of 85% with gel column in the next step.
(II) gel column separation and purification
Repeatedly purifying the carnosol component containing about 85 wt% obtained in the step (one) by using hydroxypropyl dextran gel (Sephadex LH-20 gel). The length of the gel column is 150cm, and the gel column is filled and loaded by a wet method. The mobile phase was eluted with chloroform/methanol 2.5: 1 (vol/vol) at a flow rate of 5ml/min for a chromatography time of 490 min. The same components are combined, and the mixture is decompressed and evaporated to dryness to obtain 41.5g of carnosol with high content of more than or equal to 98 percent.
(III) HPLC detection
HPLC detection is carried out on the carnosol obtained in the step (II), and the result is shown in the attached figure 1.
Liquid chromatograph: waters 2545 model 2998 detector
A chromatographic column: waters Xbridge TM Shield RP 18 Column (4.6 x 250mm, 5 μm)
Flow rate: 1mL/min
Detection wavelength: 284nm
Sample introduction amount: 10 μ l
Preparing solution of a test sample and a reference sample: chromatographic grade methanol dissolution
Detecting the mobile phase of carnosol: 70: 30: 3 thousandths of methanol, water and glacial acetic acid
The sethoxydim peak emergence time: 13.76min
(IV) measurement of one-dimensional nuclear magnetic resonance Spectroscopy
Detecting the carnosol sample with the content of more than or equal to 98% obtained in the step (II) by using an INOVA-500 nuclear magnetic resonance instrument (Varian corporation, USA) to obtain one-dimensional nuclear magnetic hydrogen spectrum and carbon spectrum data, and the result is shown in attached figure 2 and figure 3.
1. Spectral data of carnosol
1H-NMR(DMSO，500MHz)δ：0.78(3H，s，H-18)，0.81(3H，s，H-19)，1.12(3H，d，J＝7.0Hz，H-16)，1.23(3H，d，J＝7.0Hz，H-17)，3.22(1H，m，H-15)，5.46(1H，s，H-7)，6.70(1H，s，H-14)；
13C-NMR(DMSO，100MHz)δ：28.81(C-1)，18.57(C-2)，40.55(C-3)，34.18(C-4)，47.87(C-5)，29.26(C-6)，76.95(C-7)，134.25(C-8)，131.57(C-9)，44.95(C-10)，143.30(C-11)，143.07(C-12)，121.87(C-13)，111.28(C-14)，26.20(C-15)，22.82(C-16)，22.69(C-17)，31.38(C-18)，19.44(C-19)，175.54(C-20)。
Comparing with the known literature, the structure of the carnosol is finally confirmed.
Example 3 preparation of high purity carnosol from Rosmarinus officinalis extract
Normal phase silica gel column separation and purification
The carnosol component with the content of about 85 percent is obtained by adopting the same method as the step (one) of the example 2.
(II) gel column separation and purification
Repeatedly purifying the carnosol component containing about 85 wt% obtained in the step (one) by using hydroxypropyl dextran gel (Sephadex LH-20 gel). The length of the gel column is 120cm, and the gel column is filled and loaded by a wet method. The mobile phase was eluted with chloroform/methanol at 2: 1 (volume ratio) at a flow rate of 3ml/min for a chromatography time of 500 min. Mixing the same components, and evaporating to dryness under reduced pressure to obtain 40.8g of carnosol with high content of more than or equal to 98%.
(III) HPLC detection
And (3) respectively carrying out HPLC detection on the carnosol obtained in the step (II), wherein the detection conditions are the same as those in the step (III) in the example 2, and the peak time of the carnosol is similar to that in the example 2.
Example 4 preparation of high purity carnosol from Rosmarinus officinalis extract
Normal phase silica gel column separation and purification
The carnosol component with the content of about 85 percent is obtained by adopting the same method as the step (one) of the example 2.
(II) gel column separation and purification
Repeatedly purifying the carnosol component containing about 85 wt% obtained in the step (one) by using hydroxypropyl dextran gel (Sephadex LH-20 gel). The length of the gel column is 150cm, and the gel column is filled and loaded by a wet method. Eluting with petroleum ether, chloroform and methanol at volume ratio of 5: 1, wherein the flow rate of the mobile phase is 6ml/min, and the chromatography time is 490 min. The same components are combined, and the mixture is decompressed and evaporated to dryness to obtain 41.3g of carnosol with high content of more than or equal to 98 percent.
(III) HPLC detection
And (3) carrying out HPLC detection on the carnosol obtained in the step (II), wherein the detection conditions are the same as those in the step (III) in the example 2, and the result shows that the peak time of the carnosol is similar to that in the example 2.
Example 5 preparation of high purity carnosol from Rosmarinus officinalis extract
Normal phase silica gel column separation and purification
The carnosol component with the content of about 85 percent is obtained by adopting the same method as the step (one) of the example 2.
(II) gel column separation and purification
Repeatedly purifying the carnosol component containing about 85 wt% obtained in the step (one) by using hydroxypropyl dextran gel (Sephadex LH-20 gel). The length of the gel column is 150cm, and the gel column is filled and loaded by a wet method. Eluting with petroleum ether, chloroform and methanol at volume ratio of 2: 1, wherein the flow rate of the mobile phase is 5ml/min, and the chromatography time is 500 min. The same components are combined, and the mixture is decompressed and evaporated to dryness to obtain 41.2g of carnosol with high content of more than or equal to 98 percent.
(III) HPLC detection
And (3) respectively carrying out HPLC detection on the carnosol obtained in the step (II), wherein the detection conditions are the same as those in the step (III) in the example 2, and the peak time of the carnosol is similar to that in the example 2.
Comparative example 1 dissolution test of rosemary extract
Six portions of the rosemary extract prepared in example 1 were weighed out, 10g portions were divided into six groups, each group was dosed with 100 ml: ultrasonically dissolving petroleum ether, chloroform, ethyl acetate, acetone, 80% ethanol and water saturated ethyl acetate for 0.5 h, filtering to remove insoluble substances, concentrating the filtrate under reduced pressure to obtain extract, weighing, detecting and calculating the content of carnosol.
The specific grouping operation is as follows:
a first group: dissolving 10g herba Rosmarini officinalis extract in 100ml petroleum ether under ultrasonic for 0.5 hr, filtering to remove insoluble substances, and concentrating the filtrate under reduced pressure to obtain extract 3.9g, carnosol content is 14.15%, and calculating carnosol absolute content is 0.5519 g. The petroleum ether cannot completely dissolve the carnosol in the extract.
Second group: dissolving 10g herba Rosmarini officinalis extract with 100m1 chloroform under ultrasonic for 0.5 hr, filtering to remove insoluble substances, and concentrating the filtrate under reduced pressure to obtain extract 5.0g, carnosol content is 15.10%, and calculating absolute content of carnosol to be 0.7550 g. Chloroform dissolution does not completely dissolve the carnosol in the extract.
Third group: dissolving 10g herba Rosmarini officinalis extract with 100m ethyl acetate 1 for 0.5 hr, filtering to remove insoluble substances, and concentrating the filtrate under reduced pressure to obtain extract 5.6g, which contains carnosol 16.01% and calculated as absolute carnosol 0.8966 g. The carnosol in the extract cannot be completely dissolved out even if the ethyl acetate is dissolved.
And a fourth group: dissolving 10g herba Rosmarini officinalis extract in 100ml acetone under ultrasonic for 0.5 hr, filtering to remove insoluble substances, and concentrating the filtrate under reduced pressure to obtain extract 6.0g, carnosol content is 15.87%, and absolute carnosol content is calculated to be 0.9522 g. Acetone is dissolved, and the carnosol in the extract cannot be completely dissolved out.
And a fifth group: dissolving 10g herba Rosmarini officinalis extract in 100ml 80% ethanol under ultrasonic for 0.5 hr, filtering to remove insoluble substances, and concentrating the filtrate under reduced pressure to obtain extract 6.5g, carnosol content is 15.42%, and calculating carnosol absolute content to be 1.0023 g. Dissolving with 80% ethanol to completely dissolve carnosol in the extract.
A sixth group: dissolving 10g herba Rosmarini officinalis extract in 100ml water saturated ethyl acetate under ultrasonic condition for 0.5 hr, and concentrating the filtrate under reduced pressure to obtain extract 6.3g, wherein the carnosol content is 16.27%, and the calculated absolute content of carnosol is 1.0250 g. Dissolving with water saturated ethyl acetate, can completely dissolve carnosol in the extract, remove large polar impurities to the utmost extent, and recover solvent easily.
Claims (5)
1. A method for preparing high purity carnosol, comprising the steps of:
I. dissolving herba Rosmarini officinalis extract with water saturated ethyl acetate, filtering, and removing insoluble substances;
mixing the filtrate with normal phase silica gel, loading the filtrate on a column by a dry method, loading the filtrate by a dry method, and mixing the filtrate with chloroform: methanol: carrying out gradient elution on acetic acid (100-95): (0-5): 0-1 ‰), and combining the same components to obtain 5 components, wherein the components are respectively: a small polar impurity part, a carnosol crude product, a carnosic acid crude product, a component with the main component of ursolic acid and a large polar impurity part;
2. The method of claim 1, wherein the rosemary extract is an aqueous ethanol extract of rosemary flowers or leaves.
3. The process according to claim 1, wherein the gradient elution in step I is carried out in five times, with the mobile phases being, in order: chloroform; chloroform, methanol and acetic acid, wherein the volume ratio is 100: 0: 1 per mill; chloroform, methanol and acetic acid, wherein the volume ratio is 100: 1: 1 per mill; chloroform, methanol and acetic acid, wherein the volume ratio is 100: 2: 1 per mill; chloroform, methanol and acetic acid, wherein the volume ratio is 95: 5: 1 per mill.
4. The method of claim 1, wherein said steps
The length of the middle hydroxypropyl sephadex column is 120-150 cm; loading columns by a wet method, and loading samples by the wet method; the flow rate of the mobile phase in the hydroxypropyl dextran gel is 2-6 ml/min.
5. Method according to any one of claims 1 to 4, characterized in that said steps
The volume ratio of the medium mobile phase is as follows: chloroform: methanol = 2.5: 1, or petroleum ether: chloroform: methanol = 5: 5: 1.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102599610A (en) * | 2012-03-15 | 2012-07-25 | 长沙雅莹生物科技有限公司 | Preparation method of rosemary extracts |
| CN103319495A (en) * | 2013-07-20 | 2013-09-25 | 高政 | Preparation method of high-purity carnosol |
| CN105669432B (en) * | 2016-03-10 | 2017-12-12 | 河南中大恒源生物科技股份有限公司 | A kind of method of comprehensive extraction carnosic acid carnosol and ursolic acid |
| CN107502451A (en) * | 2017-09-13 | 2017-12-22 | 河南森源本草天然产物股份有限公司 | The preparation method of Rosmarinus officinalis extract |
| CN107513095A (en) * | 2017-09-18 | 2017-12-26 | 中南林业科技大学 | A kind of preparation method of Rosmarinus officinalis extract |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1259043C (en) * | 2003-09-26 | 2006-06-14 | 上海市新文达生物科技有限公司 | Application of salvia acid in pharmacy |
-
2018
- 2018-01-30 CN CN201810092815.5A patent/CN108358945B/en active Active
- 2018-01-30 CN CN202010482363.9A patent/CN111440184B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102599610A (en) * | 2012-03-15 | 2012-07-25 | 长沙雅莹生物科技有限公司 | Preparation method of rosemary extracts |
| CN103319495A (en) * | 2013-07-20 | 2013-09-25 | 高政 | Preparation method of high-purity carnosol |
| CN105669432B (en) * | 2016-03-10 | 2017-12-12 | 河南中大恒源生物科技股份有限公司 | A kind of method of comprehensive extraction carnosic acid carnosol and ursolic acid |
| CN107502451A (en) * | 2017-09-13 | 2017-12-22 | 河南森源本草天然产物股份有限公司 | The preparation method of Rosmarinus officinalis extract |
| CN107513095A (en) * | 2017-09-18 | 2017-12-26 | 中南林业科技大学 | A kind of preparation method of Rosmarinus officinalis extract |
Non-Patent Citations (5)
| Title |
|---|
| High-performance liquid chromatographic determination of carnosic acid and carnosol in Rosmarinus oficinalis and Salvia oficinalis;Nobuyuki Okamura，等;《Journal of Chromatography A》;19840923;第679卷(第2期);381-386 * |
| One-step isolation of carnosic acid and carnosol from rosemary by centrifugal partition chromatography;Mary H. Grace，等;《J. Sep. Sci.》;20171231;第40卷;1057-1062 * |
| 迷迭香抗氧化活性及其作用机理研究和天然抗氧化保健品的研制;黄纪念;《中国博士学位论文全文数据库 工程科技Ⅰ辑》;20030915;全文 * |
| 迷迭香抗氧化活性研究;陈如;《上海大学硕士学位论文》;20060710;第27-29页 * |
| 迷迭香精油及抗氧化剂的提取纯化研究;肖香;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20070215;全文 * |
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